“You lookin’ for Pizzarelli’s house?” John Pizzarelli is grinning expectantly in front of his home on Manhattan’s Upper West Side. He’s rarely seen out of a fine tailored suit, but today he opts for a gray V-neck sweater and … wait for it … a Red Sox cap. This, from a proud native of northern New Jersey?

“I rooted for the Yankees until they fired Dick Howser in ’82,” says the guitarist and vocalist, sitting down inside. (It was 1980, in fact.) “Only the Yankees could fire a guy who won 103 games. It wasn’t enough for them. … I’m part of a group called the BLOHARDS, the Benevolent and Loyal Order of Honorable Ancient Red Sox Diehard Sufferers. It’s all these displaced New Englanders and Yankee-haters who get together at the Yale Club when the Red Sox come to town.” On Pizzarelli’s website, there’s even a video of him singing the national anthem at Fenway Park.

When it comes to music, Pizzarelli is just as avid but maybe less fiercely partisan. He’s deeply grounded in swing-style jazz—a commitment handed down from his father, the master seven-string guitarist John “Bucky” Pizzarelli, now 86 and still his son’s frequent duo partner. But from early on, the younger John digested rock and pop and looked at music with a broader view. His new Telarc release, Double Exposure, includes music by Donald Fagen, Neil Young, Billy Joel, Tom Waits, the Allman Brothers and other ’70s-’80s touchstones, mashed up in different ways with classics by the likes of Lee Morgan, Joe Henderson and Wes Montgomery.

For many years Pizzarelli favored a lean trio lineup with no drums, but his recent Telarc outings tend to feature expanded ensembles and guests. Double Exposure revolves around a working quartet with bassist and younger brother Martin Pizzarelli, pianist Larry Fuller and drummer Tony Tedesco. There’s a supporting cast of four horns, organ, violin and a supplemental vocal from Jessica Molaskey, John’s wife—“the brains of the operation,” he says, just as she enters the room.

The earlier trio, with Martin on bass and the outstanding Ray Kennedy on piano, was documented on P.S. Mr. Cole (a follow-up to 1995’s Dear Mr. Cole with Benny Green and Christian McBride), Kisses in the Rain and Live at Birdland. Modeled closely on Nat King Cole’s trio with guitarist Oscar Moore, this unit offered everything from crawling ballads to “tempos I can’t even play anymore,” as Martin Pizzarelli jests. On speed-demon numbers like “I’m an Errand Boy for Rhythm” and “I Know That You Know,” Pizzarelli threw down the gauntlet as a jazz guitar virtuoso. His percussive and unfaltering rhythm chops, densely packed chord solos and nimble single-note work (augmented by laser-accurate scat singing) made clear that Pizzarelli, having learned his father’s lessons well, could stand up against any archtop player in the business. (Kennedy, unable to handle constant touring, stepped aside in 2005.)

Of course there’s also Pizzarelli the crooner, the cutting humorist, the headliner at upscale venues like Café Carlyle, a man suave enough to open for Frank Sinatra on a European tour in the early ’90s. “We played for 20,000 people in Hamburg,” Pizzarelli recalls. “In Stuttgart, we were in the middle of the damn town. It’s like, Sinatra doesn’t play venues, he just plays the city. They build a stage and everybody shows up. I was on RCA at the time and a guy from the BMG group [suggested me for the gig]. They couldn’t find a German comic or singer they liked. So I brought my quartet, we’d come on and play, we’d go off and two minutes later Sinatra would walk out. For the last number you’d look in the wings and there was Sinatra.”

Other major collaborations include Rosemary Clooney, Natalie Cole, James Taylor and most recently Paul McCartney, whose new standards album Kisses on the Bottom (Hear) features Pizzarelli in a significant role. But amid all the high-profile jobs, Pizzarelli continues to record for smaller labels like Challenge and Arbors, making albums with a more casual and intimate feel, and often more guitar. His duo dates with young violinist Aaron Weinstein (Blue Too, 2007) and fellow seven-string guitarist and singer Davy Mooney (Last Train Home, 2009) are unheralded gems.

Blue Too, inspired by Bucky’s work with Joe Venuti in the Blue Four, is a veritable “guitar master class” in Weinstein’s estimation. “There’s no record that better displays John’s complete mastery of his instrument,” the violinist argues, not implausibly. “And how many people in John’s position would willingly sit with a 20-year-old kid and genuinely consider his ideas? There’s no ego in that.”

Of course, a musician who has apprenticed with a famous father, opened for Sinatra and accompanied McCartney has a wealth of experience not being the star. It puts Pizzarelli in a good position to give back, even as he continues exploring and connecting the different aspects of his artistry.

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Born in 1960, John Pizzarelli is the third in a line—Bucky’s father was also named John. (Pizzarelli’s college-age son is John the fourth.) Mary Pizzarelli, one of John’s two older sisters, played classical guitar and even appeared on a couple of records with Bucky as a teenager. “She’s the only one who studied formally with my father, which is why she works for a major corporation today,” Pizzarelli deadpans.

Starting on tenor banjo at age 6, John received early instruction from his great uncles, Peter and Bobby Domenick, who had taught Bucky as well. “My younger uncle Bobby played with a whole gang of bands,” the elder Pizzarelli says. “Bob Chester, Buddy Rogers, Frank Bailey, Raymond Scott. He was forever coming home with a brand new suit and a brand new car and a big Super 400 Gibson. I said to my son, ‘That’s what I wanna do.’”

For six years John stuck to banjo. “I was playing songs like ‘Bye Bye Blues’ and ‘Yes Sir, That’s My Baby’ when I was like 8,” he recalls. “If Bucky and Pete and Bobby all played along, you sounded like you were a king. Every guy played an inversion, and you’re sitting there going, ‘Geez, this is ridiculous, this is the swingingest thing I ever heard.’ And they had you surrounded. You’re just sitting there playing 4/4 and everybody else has something crazy going on. You couldn’t believe you were playing this very simple thing, yet all this music was happening around you.”

He continues: “Later, when I would take lessons with Pete on Sundays, at the end my father would grab a guitar and I’d listen to them play. I could never figure out how they knew what they were doing. It was the coolest thing, and they were just fakin’ stuff, sitting there smiling. The spirit of that playing is something that sticks with you your whole life. That’s what you strive for, to have that kind of fun.”

Soon Pizzarelli switched to guitar. “I already had the calluses,” he remembers. “I sat next to my father, just watched and listened, learned things off of records. I learned theory along the way from good arrangers, but it’s not as good as it could be.” In the late ’60s, Bucky adopted the seven-string guitar, an instrument pioneered by George Van Eps, and John would later make the switch as well. Before he knew it there were gigs with dad, playing guitar and singing in a duo that still persists. “Bucky coached John on singing in the beginning,” according to Ray Kennedy. “He always used to say, ‘Don’t try to sing too loud—sing soft, and take your time.’ I think that’s what John based [his style] on.”

For a time John rehearsed with rock bands at the family home. “He had a garage full of amplifiers,” Bucky remembers, “and every time they rehearsed the cops would come.” It’s poetic that decades later, John brought Bucky along for the McCartney session. “Paul said we’d do the two guitars, so we did ‘It’s Only a Paper Moon’ together,” Bucky recalls. “Oh, it came out great. I never thought I’d be playing with a Beatle. He was the best artist I ever worked with, and I played with everybody.”

In a supplemental McCartney webcast for iTunes Live, John took the first chorus of “Paper Moon” with fellow guitarist Anthony Wilson (son of legendary bandleader and composer Gerald Wilson). He also backed McCartney alone on the introductory verses to “Home (When Shadows Fall),” “More I Cannot Wish You” and “Always.” “It’s just elegant and beautiful,” Wilson comments, “perfect for that rich, seven-string chordal thing that John can do so well. And I love the way he uses those ribbon flatwound strings. It has that wonderful, rolled-off kind of sound.”

Perhaps the McCartney gig was fated from the moment of John Pizzarelli Meets the Beatles in 1998. It was on that Beatles tribute that Pizzarelli first ventured the mashup idea—the merging of two entirely different songs—that figures so prominently on Double Exposure. Interesting, too, that just as Pizzarelli is delving into classic rock repertoire, McCartney chooses to address the ’20s-’40s songbook that is Pizzarelli’s birthright.

Needless to say, Sir Paul is only the latest pop/rock icon to flirt with standards. But his attempt, unlike many others, succeeds in foregrounding lesser-known songs and capturing a real band sound. The iTunes webcast features Pizzarelli and Wilson with pianist Diana Krall, bassist John Clayton, drummer Karriem Riggins and others. “Paul’s thing has an interesting arc to it,” Pizzarelli maintains. “They let us play jazz on it, and there were really good musical choices. It’s a real live record.”

Wilson, for his part, contends that Kisses on the Bottom “has been wrongly maligned for being too pleasant, but I think that misses what it means to reclaim these old songs and old dance tempos. I think that’s subversive now. Paul was interested in reaching back to this other time, and it made John and Bucky the perfect choice. There’s this other art that stays in the shadows—knowing verses, really knowing where the changes can go and be correct, with the right voice-leading—that doesn’t get talked about that much. John is one of those players. He can accompany and play time, he can play a perfect verse that doesn’t need any bells and whistles to be beautiful. We have a shared love of the old, old tradition—I guess it comes from having fathers who were in it. There’s a lot that filters down there.”

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Pizzarelli grabs his nearest instrument and starts plucking chords to “What a Fool Believes” and “It Keeps You Runnin’,” by the Doobie Brothers. Later he plays a riff from Steely Dan’s “Time Out of Mind.” “It used to be that the songbook went to 1964,” he reflects, “and then you had Marilyn and Alan Bergman and Dave Frishberg and a few other people who continued. But now we realize that all this [later] music is there, that there are songs we can use. That’s what jazz is, taking a song and translating it into your voice.” (John draws on insights like these not just as a performer, but also a radio host: Since late 2005 he and Jessica have co-hosted Radio Deluxe, a two-hour show in national syndication, with in-person guests ranging from Liza Minnelli to Kurt Elling.)

Singling out some favorites, Pizzarelli lauds Michael McDonald for helping raise the harmonic sophistication of pop radio in the ’70s: “And Steely Dan, Joni Mitchell—there were these people breaking the barrier, and it was great ear training for me to learn all that stuff. I went to the University of Tampa and I was by myself for a year down there with a boombox in my room, with all these cassettes I had made in New Jersey, and I would sit and listen to Pat Metheny’s white album [Pat Metheny Group, 1978] and [Steely Dan’s] Aja all the time and say, ‘What is that they’re doing?’ [Plays a figure from Steely Dan’s ‘Black Cow’] I thought the Gaucho record was even better. I’ll never forget listening to the entire Nightfly record [by Donald Fagen]; it’s about a guy growing up in the ’50s in New Jersey, and [Double Exposure] is the same idea in a sense.” (After Tampa, Pizzarelli briefly attended William Paterson University but never received a degree, moving instead into his father-son collaborations and ultimately a solo career.)

Forging links between jazz and the wider musical world is a prevalent theme today, and Pizzarelli has his own natural approach to it. On Desert Island Dreamers, a 2010 album by the Pizzarelli Boys (a band centered around John, Bucky and Martin), there’s a cover of “Stairway to Heaven” that really shouldn’t work, but does: It’s a convincing ballad and a vamp vehicle, with moments that recall “Just the Two of Us.”

On Double Exposure, Donald Fagen’s “Walk Between the Raindrops” translates with no problem into a jazz context, and there’s a nicely executed homage to Thad Jones’ “Tiptoe” courtesy of famed arranger and frequent Pizzarelli colleague Don Sebesky. Similarly, on the Michael McDonald ballad “I Can Let Go Now,” Sebesky weaves in the opening chordal pattern of Claude Thornhill’s “Snowfall,” a remarkably snug fit. Opinions will differ on the jarring juxtaposition of Tom Waits’ “Drunk on the Moon” with Billy Strayhorn’s revered “Lush Life.” But to borrow a phrase from Elvis Costello’s “Alison” (also on the disc), Pizzarelli’s aim is true. Simply put, he’s quoting, putting different ideas in new contexts—a time-honored practice in jazz. “We hope,” he says.

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Jazz has always danced along the putative line between art and entertainment, and Pizzarelli, much like his idol Nat Cole, has embodied that tension ever since he debuted in 1983 with I’m Hip—Please Don’t Tell My Father. “People sometimes say, ‘Oh, well, Pizzarelli’s obviously trying to make a commercial record,’” he remarks. “Well, everybody wants their records to sell. What are you, stupid? You do what you do so people will show up. My goal is to play the best music I can and to entertain the people who come to hear it. You’re damn right I tried to make a commercial record. I don’t think it was at the expense of the music, though.”

It helps that Pizzarelli is a fish in water onstage, with great comic timing and rapier wit. “From the first job I played with him to the last,” says Ray Kennedy, “I pretty much laughed the whole time. And I’m a real cynic.” Joking with the crowd isn’t just incidental filler for Pizzarelli, but “part of the show.” “It’s this thing, because when you talk it throws all the jazz guys off. If we just went and did what we did, they’d say, ‘Oh, they’re a jazz act, look at them go.’ But if you talk, then all of a sudden it’s a cabaret act. I’ve always felt that you’ve got to talk. I spent my teenage years watching jazz guys play and nobody said anything. I sat there for an hour and loved what I heard, but nobody said hello. You’re expected to know what they’re playing. My view is that there’s always a first-timer in the audience.”
This deep-seated populism, coupled with Pizzarelli’s largely traditional style, might lead some to see his talent as circumscribed, when in fact he is “comfortable in just about any realm,” Kennedy says. “We went to Berklee one day, and the students wanted to know if John ever played anything that was more [modern]. … John started playing lines that would rival all the great harmonic guys. Not only that, but he sang along with it. He’s a little bit humble with that kind of stuff. He does great things in concert and he’s so successful with that, but there’s a part of him that’s even more advanced and creative. He’s got more talent than you’ll ever see.”